Overview

Your Trek Travel guides will meet you at the Palazzo Montebello at 11:00 AM on the first day of your luxurious bike tour in Tuscany. After a one-hour shuttle, you will arrive at the quiet and historic Badia a Coltibuono, or "Abbey of the Good Harvest," to have a local lunch with stunning views of the Chianti hills. Your Trek Travel guides will then spend some time familiarizing you with your Trek bicycle and ensuring you have an excellent fit. A warm-up ride will take you along picturesque, winding roads through woodlands and ancient olive groves. You’ll arrive at our serene hotel, Pieve Aldina, part of the renowned Relais & Châteaux collection, where you will be hosted for the next three nights. This evening, you'll enjoy a warm welcome as we gather for drinks on the terrace overlooking Tuscan vineyards before enjoying the first of many exquisite meals together, this one expertly prepared at the hotel's convivial enoteca and where you can surrender your taste buds to Chef Niccolo Pini's cuisine, inspired by the seasons.

Overview

Take in the tranquil surroundings of Pieve Aldina before a day's riding through forested hills and olive groves begins. Pedal through the village of Lecchi and stop for an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti, a compact hilltop town of art galleries, cycling boutiques, and wine shops worth a proper wander. Lunch is yours to choose from the local trattorias and pavement cafés lining the cobbled streets, bruschetta, caprese, and other Tuscan staples served at your own pace. From here, a short climb returns you to the hotel, where the pool and the afternoon are yours, or add a loop to the village of Lucarelli if the legs are willing. This evening, a shuttle takes you to Castello di Volpaia, where the Mascheroni Stianti family welcome you personally for a private visit to their winery and original olive oil press, followed by an intimate tasting from the cellars and a wine-paired dinner in their family villa.

Overview

After a leisurely breakfast buffet on the terrace—fresh local produce, Tuscan pastries, and house-made specialities—the ride threads through Chianti vineyards with panoramic views of rolling Tuscan hills. A stop at Castello di Brolio, the oldest castle and winery in the area and in the Ricasoli family for nearly 800 years, is as much a history lesson as it is a ride break. Pause for an espresso at the Eroica Caffè, named after L'Eroica, the celebrated local cycling event on the strade bianche, where riders take to white gravel roads in full vintage regalia. Lunch is at Osteria alla Villa in the village of Villa a Sesta, a small bistro known for its hospitality and fresh, creative Tuscan dishes. The afternoon is yours: climb into the hills to Monteluco, one of the highest points in Chianti, or return to the hotel to restore at the spa or take a slow hour by the pool with an Aperol Spritz. This evening, a short shuttle takes you back to the hilltop town of Radda in Chianti for dinner at a restaurant of your choice, a quiet table with your travel partner or a convivial one with new friends.

Overview

Today the Val d'Elsa (Elsa Valley) opens up as you descend from the hills of Chianti. Forested ridgelines give way to quiet country lanes lined with golden hillsides dappled with silver olive groves and dark cypress trees. The landscape shifts gradually as you make your way toward Castello di Casole, a former estate of 10th-century nobility and one of Italy's most celebrated destination hotels. Along the way, a farm-to-table picnic lunch features hand-cured prosciutto, local cheeses, and cold-pressed extra virgin olive oil from the surrounding groves. Afterward, choose to climb to the medieval village of Simignano or ride directly to the castle, where the hotel terrace and a cocktail await before dinner with far-reaching views over the Tuscan countryside.

Overview

A castle estate perched above the Val d'Elsa makes for an unhurried start to the final riding day. After breakfast, descend from the castle into the valley below, across vine-covered slopes and up to the medieval town of San Gimignano, where the legendary open-air market fills the streets with the colorful stalls of local artisans and producers. Taste fresh regional olives, browse the craft vendors, and choose an osteria of your own for lunch. The afternoon brings you back to the hotel, where the infinity pool overlooks the Val d'Elsa, the spa invites a longer stay, and a ceramics or watercolor class is there for those who want it. Tonight, a private pizza-making class with a trained pizzaiolo puts you behind the counter, spinning your own dough and building the pie exactly as you like it. Raise a glass to a week in Tuscany's wine country—there is no better place to toast it than here.

Overview

This morning presents an early start for those taking the final loop ride through the Tuscan countryside as the light breaks. For those who'd rather, the breakfast patio and a hot cappuccino offer their own kind of farewell. Say goodbye to your guides at 11:00 AM before boarding the private shuttle back to Palazzo Montebello in Florence, as the rest of your travel adventures lie ahead.